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  • 11
    Electronic Resource
    Electronic Resource
    Male pheromone of swift moth,Hepialus hecta L. (Lepidoptera: Hepialidae) (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 3511-3521 
    Details
    ISSN: 1573-1561
    Keywords: Hepialus ; Lepidoptera ; Hepialidae ; swift moth ; pheromone ; dihydropyrone ; 2,9-dioxabicyclo[3.3.1] nonane ; behavior ; electrophysiology
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (R)-6-Ethyl-2-methyl-2,3-dihydro-4H-pyran-4-one, (1R,3S,5R)-3-ethyl-1,8-dimethyl-2,9-dioxabicyclo[3.3. 1]non-7-ene, and (1R,3S,5R)-3-ethyl-1,8-dimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-one represent the main components in the male pheromone of the swift moth,Hepialus hecta. The amounts of the three components were 40, 5, and 5 μg per male, respectively. Structure elucidation of the compounds was based on spectroscopic data as compared to synthetic reference samples. The absolute configurations were determined by gas chromatography on chiral stationary phases; optically active samples served as reference compounds. Electrophysiological and behavioral experiments with natural material and synthetic samples clearly showed the three heterocyclic compounds to act as pheromones. (E, E)-α-Farnesene represents the main component of the scent secretion of maleHepialus humuli.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00982114
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  • 12
    Electronic Resource
    Electronic Resource
    Chemistry of Leichhardt's Grasshopper, Petasida ephippigera, and its Host Plants, Pityrodia jamesii, P. ternifolia, and P. pungens (2000)
    Springer
    Journal of chemical ecology 26 (2000), S. 2275-2290 
    Details
    ISSN: 1573-1561
    Keywords: Leichhardt's grasshopper ; Petasida ephippigera ; Pityrodia jamesii ; Pityrodia ternifolia ; Pityrodia pungens ; hydroxycineole ; dihydrochalcone ; chalcone ; sesquiterpene glycoside ; aposematic
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Investigation of the strikingly aposematic Leichhardt's grasshopper revealed a number of host-plant-derived components. Chemical study of the three known host plants revealed a diverse array of components. Pityrodia ternifolia and P. pungens contain predominantly sesquiterpenes and sesquiterpene glycosides and P. jamesii is rich in cineole, dihydrochalcones, chalcones, and monoterpene glycosides. Feces from grasshoppers feeding on P. jamesii contain a mixture of hydroxycineoles, of which 3α-hydroxycineole is the predominant isomer (68%). No evidence for previously suspected "alkaloidal" toxins was found in either the insect or host plant.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1005518625764
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  • 13
    Electronic Resource
    Electronic Resource
    Andrena wilkella male bees discriminate between enantiomers of cephalic secretion components (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 429-441 
    Details
    ISSN: 1573-1561
    Keywords: Enantiomer discrimination ; male patrolling ; odor marking ; Hymenoptera ; Apoidea ; Andrena wilkella ; bee ; EAG ; spiroacetal ; absolute configuration ; 2,8-dimethyl-1,7-dioxaspiro[5.5]undecane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Diastereomers of the spiroacetal, 2,8-dimethyl-1,7-dioxaspiro [5.5]undecane, represent main components of the cephalic secretion from males of the solitary bee,Andrena wilkella. The major compound proved to be of high enantiomeric purity, showing (2S,6R,8S) configuration. Only the naturally occurring enantiomer attracted patrolling males in the field; its antipode was behaviorally inactive and in a racemic mixture did not inhibit response. The (E,Z) diastereomers were also found to be almost inactive. EAG studies gave the same result as the behavioral tests. The biological function of the spiroacetal is discussed in view of the evolution of the mating behavior inA. wilkella.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01021775
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  • 14
    Electronic Resource
    Electronic Resource
    New technique for the determination of interconversion processes based on capillary zone electrophoresis: Studies with axially chiral biphenyls (1996)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 8 (1996), S. 441-445 
    Details
    ISSN: 0899-0042
    Keywords: capillary zone electrophoresis ; axially chiral biphenyls ; energy barrier ; cyclodextrin derivatives ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new technique is presented for the investigation of the rotational energy barrier of axially chiral biphenyls, based on capillary zone electrophoresis using cyclodextrin derivatives as chiral selectors. Only minute amounts are required for the investigation of dynamic processes with energy barriers of 100-130 kJ/mol. The influence of the chiral selector on the conformational stability of atropisomers can be determined separately for each enantiomer. Additionally, segmentation of the capillary into different buffer zones allows us to exclude any influence of the chiral selector on the rotational energy barrier. © 1996 Wiley-Liss, Inc.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
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  • 15
    Electronic Resource
    Electronic Resource
    Enantioselective capillary gas chromatography in the investigation of stereochemical correlations of terpenoids (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 499-504 
    Details
    ISSN: 0899-0042
    Keywords: enantioselective capillary gas chromatography ; cyclodextrin derivatives ; stereochemistry of terpenes ; monoterpenes ; essential oils ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Capillary gas chromatography employing the unique selectivities of specifically substituted cyclodextrins is highly suited for stereochemical investigations of terpenoid compounds. The analysis of many essential oils have shown that monoterpene derivatives regularly occur as enantiomeric mixtures. In the case of sesquiterpene hydrocarbons, liverworts (Hepaticae) and other lower organisms usually biosynthesize compounds of opposite stereochemistry as compared to higher plants and enantiomeric mixtures occur only occasionally. The investigation of diterpene hydrocarbons has so far shown no indication of the presence of both enantiomers in the same plant. Chirality 10:499-504, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
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  • 16
    Electronic Resource
    Electronic Resource
    Enantioselective and nonenantioselective degradation of organic pollutants in the marine ecosystem (1993)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 5 (1993), S. 393-399 
    Details
    ISSN: 0899-0042
    Keywords: chiral capillary gas chromatography ; chiral high-performance liquid chromatography ; stationary cyclodextrin phases ; chiral pollutants ; enantioselective processes ; microbial degradation processes ; photochemical degradation processes ; enzymatic degradation processes ; blood-brain barrier ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Enantiomeric ratios of 11 chiral environmental pollutants determined in different compartments of the marine ecosystem by chiral capillary gas chromatography and chiral high-performance liquid chromatography allow discrimination between the following processes: enantioselective decomposition of both enantiomers with different velocities by marine microorganisms (α-HCH, β-PCCH, γ-PCCH); enantioselective decomposition of one enantiomer only by marine microorganisms (DCPP); enantioselective decomposition by enzymatic processes in marine biota (α-HCH, β-PCCH, trans-chlordane, cis-chlordane, octachlordane MC4, octachlordane MC5, octachlordane MC7, oxychlordane, heptachlor epoxide); enantioselective active transport through the “blood-brain barrier” (α-HCH); nonenantioselective photochemical degradation (α-HCH, β-PCCH). © 1993 Wiley-Liss, Inc.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530050522
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  • 17
    Electronic Resource
    Electronic Resource
    Determination of the absolute configuration of secondary alcohols with Horeau's method including enantioselective gas chromatography (1994)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 6 (1994), S. 141-147 
    Details
    ISSN: 0899-0042
    Keywords: Horeau's method ; configuration of secondary alcohols ; enantioselective gas chromatography ; 2-phenylbutyric acid ; cyclodextrin derivative ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of optically active secondary alcohols with excess of racemic 2-phenylbutyric acid anhydride in pyridine proceeds at different rates to the diastereoisomeric esters (kinetic partial resolution). According to Horeau the (unknown) absolute configuration of the alcohol can be derived from the optical rotation of the remaining excess of 2-phenylbutyric acid in the reaction mixture. Measuring the optical rotation may be very difficult in cases of small absolute rotation values and may be inaccurate due to the necessity to completely remove all chiral impurities. The application of Horeau's method is greatly facilitated by gas chromatographic determination of the enantiomeric ratio of the remaining 2-phenylbutyric acid after methylation using a short capillary column with heptakis(2,6-di-O-methyl-3-O-pentyl)-β-cyclodextrin as a chiral stationary phase. Baseline resolution of the enantiomers is achieved after approximately 10 min of retention time. Due to the high selectivity of capillary gas chromatography the probability of impurities in the mixture to interfere with the measurement of the enantiomeric ratio is extremely low. © 1994 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530060215
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  • 18
    Electronic Resource
    Electronic Resource
    Determination of the enantiomeric composition of mexiletine and its four hydroxylated metabolites in urine by enantioselective capillary gas chromatography (1996)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 8 (1996), S. 30-34 
    Details
    ISSN: 0899-0042
    Keywords: gas chromatography ; modified β-cyclodextrin column ; chiral separation ; assay ; mexiletine ; hydroxylated metabolites ; urine ; conjugation/deconjugation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The enantiomers of mexiletine and four of its hydroxylated metabolites were directly separated by capillary gas chromatography using a heptakis(6-O-tert-butyl-dimethylsilyl-2,3-di-O-methyl)-β-cyclodextrin column. The method was applied to the analysis of urine samples from cancer patients who were treated with racemic mexiletine as part of a study of the use of mexiletine in the relief of neuropathic pain. Samples analyzed before and after deconjugation of the urine with β-glucuronidase/arylsulfatase showed a high stereoselectivity in the formation and conjugation of these compounds. © 1996 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
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  • 19
    Electronic Resource
    Electronic Resource
    Massenspektrometrische Untersuchung von Analogen des Adenosins (1972)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 105 (1972), S. 262-272 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Mass Spectrometry of Adenosine AnaloguesThe mass spectra of 23 trifluoroacetylated analogues of adenosine differing in the sugar moiety are investigated. The α- and β-anomers show characteristic intensity differences in the molecular ion and in the fragment ions m/e 310 and 424 (in pentose derivatives) as well as in m/e 550 and 680 (in hexose derivatives). The intensity differences can be explained by steric effects. The orientation of the hydroxyl groups does not influence the fragmentation process to such a degree that it is possible to draw systematic conclusions. For the identification of conformational isomers it is necessary to measure reference spectra. The ring size of the sugar is indicated by unique but low intensity fragments at m/e 524 and 410 (in furanosides of pentose derivatives), m/e 524 and 295 (in furanosides of hexose derivatives) as well as at m/e 508 and 433 (in pyranosides of hexose derivatives). Substitution at C-1' in hexose derivatives is indicated by ions at m/e 496 and 386.
    Notes: Die Massenspektren von 23 trifluoracetylierten Adenosin-Analoga (1-23), die sich in ihrem Zuckeranteil unterscheiden, weisen bei α- und β-Anomeren charakteristische Intensitätsunterschiede beim Molekül-Ion sowie bei den Fragment-Ionen m/e 310 und 424 (bei Pentose-Derivaten) bzw. m/e 550 und 680 (bei Hexose-Derivaten) auf. Die Intensitätsunterschiede lassen sich durch sterische Effekte erklären. Die Orientierung der Hydroxylgruppen beeinflußt die Fragmentierung nicht in dem Maße, daß eine systematische Zuordnung möglich ist. Für die Identifizierung der Konformationsisomeren ist die Aufnahme von Vergleichsspektren nötig. Die Ringgröße der Zucker ist durch das Auftreten von einzigartigen, allerdings wenig intensiven Fragment-Ionen bei m/e 524 und 410 (bei Furanosiden der Pentose-Derivate), m/e 524 und 295 (bei Furanosiden der Hexose-Derivate) und m/e 508 und 433 (bei Pyranosiden der Hexose-Derivate) erkennbar. Substitution an C-1' ist bei Hexose-Derivaten durch die Ionen m/e 496 und 386 gekennzeichnet.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19721050128
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  • 20
    Electronic Resource
    Electronic Resource
    Stoffwechselprodukte von Mikroorganismen, 117. L-Arginyl-D-allo-threonyl-L-phenylalanin, ein Aminosäure-Antagonist aus dem Pilz Keratinophyton terreum (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 816-825 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Metabolic Products of Microorganisms, 117. L-Arginyl-D-allo-threonyl-L-phenylalanine, an Amino Acid Antagonist from the Fungus Keratinophyton terreumAn antibiotically active tripeptide was isolated from laboratory cultures of the dermatophyte Keratinophyton terreum. Inhibitory effects have been observed on fungi (Paecilomyces varioti, Mucor miehei) but not on bacteria (Bacillus subtilis, Escherichia coll). The inhibition is antagonized by L-histidine and by L-threonine. The structure was elucidated by gas chromatographic and mass spectrometric investigations and was confirmed by comparison with synthetic L-arg-DL-allo-thr-L-phe. Synthetic L-arg-L-thr-L-phe does not show antifungal activity. Conditions for the fermentation and isolation of the antibiotic are reported.
    Notes: Aus Laboratoriumskulturen eines Dermatophyten wurde eine Substanz isoliert, die Pilze (Paecilomyces varioti, Mucor miehei), nicht aber Bakterien (Bacillus subtilis, Escherichia coli) hemmt. Die antibiotische Wirkung wird durch L-Histidin und L-Threonin aufgehoben. Die Struktur des Antibioticums wurde durch gaschromatographische und massenspektrometrische Untersuchungen als L-Argnyl-D-allo-threonyl-L-phenylalanin erkannt und durch Vergleich mit dem synthetischen Tripeptid L-Arginyl-DL-allo-threonyl-L-phenylalanin bestätigt. Synthetisches L-Arg-L-Thr-L-Phe ist antifungisch inaktiv. Bedingungen für Fermentation und Gewinnung des Antibioticums werden angegeben.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731060311
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